4-Bromo-1,5-naphthyridine

Base Information

• Chemical Name: 4-Bromo-1,5-naphthyridine
• CAS No.: 90001-34-6
• Molecular Formula: C8H5BrN2
• Molecular Weight: 209.04
• Hs Code.: 2933990090
• Mol file: 90001-34-6.mol

Synonyms:4-Bromo-1,5-naphthyridine;1,5-naphthyridine, 4-bromo-;

Chemical Property of 4-Bromo-1,5-naphthyridine

Chemical Property:

• Vapor Pressure: 0.00106mmHg at 25°C
• Refractive Index: 1.685
• Boiling Point: 311 ºC
• PKA: 1.40±0.10(Predicted)
• Flash Point: 142 ºC
• PSA: 25.78000
• Density: 1.656g/cm³
• LogP: 2.39230
• Storage Temp.: 2-8°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

4-Bromo-1,5-naphthyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Bromo-1,5-naphthyridine

There total 4 articles about 4-Bromo-1,5-naphthyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

4-hydroxy-1,5-naphthyridine (5423-54-1) → 4-bromo-1,5-naphthyridine (90001-34-6)

Guidance literature:

With phosphorus tribromide; In N,N-dimethyl-formamide; for 1.16667h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.08.109

Reference yield: 49.0%

1,5-naphthyridine (254-79-5) → 4-bromo-1,5-naphthyridine (90001-34-6)

Guidance literature:

1,5-naphthyridine; With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

With 1,2-dibromo-1,1,2,2-tetrachloroethane; In tetrahydrofuran; at -78 - 25 ℃; for 12h; regioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201703638

Reference yield:

pyridin-3-ylamine (462-08-8) → 4-bromo-1,5-naphthyridine (90001-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iodine; sulfuric acid / 1,4-dioxane; water / 15 h / 0 - 150 °C / Inert atmosphere

2.1: bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

2.2: 12 h / -78 - 25 °C / Inert atmosphere

With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex; sulfuric acid; iodine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1002/chem.201703638

upstream raw materials:

4-hydroxy-1,5-naphthyridine

1,5-naphthyridine

pyridin-3-ylamine

Downstream raw materials:

1-(2-methylbenzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea

4-amino-1,5-naphthyridine

Refernces

• 1、 McElhinny Jr., Charles J.,Lewin, Anita H.,Mascarella, S. Wayne,Runyon, Scott,Brieaddy, Lawrence,Carroll, F. Ivy. "Hydrolytic instability of the important orexin 1 receptor antagonist SB-334867: Possible confounding effects on in vivo and in vitro studies". supporting information. p. 6661 - 6664. Retrieved 2013/01/14.